Why Startups Should Hire Entrepreneurs

Hiring and assembling a good team is one of the hardest parts of business, especially for startups. It’s critical to find the “right” people that can execute and iterate quickly. For that reason, I strongly believe startups should always hire entrepreneurs.

About 5 years ago I interviewed with a creative agency in Denver. They loved my portfolio and background and the interview went extremely well up until they asked, “Do you plan to continue freelancing if you decide to work for us?” My immediate response was, “Yes.” One of the founders explained that he wants his employees to feel fresh and energized when they come to work. He wanted them to focus on this one job with them. As he continued to explain I started to doze off into a day dream, since I had already realized we were obviously not a good fit.

If I would have only focused on one job these past 10+ years I wouldn’t be where I am today. I wouldn’t have learned as much as I have. I wouldn’t have failed and succeeded at different endeavors. I wouldn’t have added as much value to the companies I have worked for. I would have been, well, a regular ole employee that waits for a paycheck and hopes for a raise or promotion every 6-12 months.

That’s NOT me. I love the grind. I’ve built businesses by myself and with others. I’ve endured the hardship of sales and marketing with no help. I know that feeling of uncertainty when your pipeline is empty and the ability to pay your mortgage is on the line. I need to work on multiple things to stay engaged and avoid boredom. For all those reasons, I bring more value to the businesses I work on than regular employees. Here’s why you should hire people like me.

Entrepreneurs Spark Fires

Hiring people who’ve never built anything themselves or taken a risk is basically hiring a task rabbit – someone who needs direction to execute. In other words, these regular employees can get things done and add value but they’ll rarely come to the table with new, innovative ideas. They are safe and conservative, since that’s what they’re used to. Companies need task rabbits. However, startups need them in moderation. Too many task rabbits can put an overwhelming amount of pressure on the leadership team.

On the other hand, hiring entrepreneurs is like hiring mini CEOs.

They’ll constantly bring fresh ideas and perspectives to the business. They’ll question the status quo at every opportunity. They’ll hammer at things relentlessly until they figure them out. They’re working constantly, even when they’re not at work! They’re wired to spark fires, and startups need this kind of spark to get off the ground and gain traction.

How to Balance an Entrepreneurial Team

One of the challenges in having an entrepreneurial team is how to balance them. We face this challenge daily at one of my startups, RxREVU. Half of us have run our own businesses or worked on other startups in the past and it shows. It shows in our meetings, our conversations, and even our products! We build complex tools for healthcare and there’s certainly no shortage of ideas or innovation in what we build. Our challenge isn’t solving technical problems, it’s deciding what to build and why.

Communication is Key

To balance this we’ve learned that we have to talk about things. We embrace new ideas and we invite everyone to listen and critique them. We don’t rely on our CEO to come up with all the answers… he has more than enough on his plate with fundraising and other leadership responsibilities, and he often runs things by us before making critical decisions. We’re still small enough (almost 15 people) that we can manage these ideas and conversations without other priorities taking a hit or exploding. We discuss things openly and make decisions collectively.

Leave your Egos at the Door

Another challenge is keeping egos in check. It’s all too easy to get caught up in prior experience and accomplishments. Our team is really good about leaving that outside our walls, and only brining it in when appropriate. For example, we don’t need to hear about your past company and its successes unless it’s relevant and contextual to something we’re doing.

The Right Tools

Furthermore, we embrace a lot of tools to keep our team connected and engaged. One of the most influential tools we use is Slack, a modern day instant message communication tool. This allows us to share ideas and have preliminary discussions before actual meetings are needed. Slack can be a dangerous time suck, but if used correctly it can add tremendous productivity, especially for teams with remote members.

How to Sniff Out the Entrepreneurs

Ok, great. I need some entrepreneurs on my team but how do I find them? What do I look for in the interview process?

Google Them!

One of the easiest ways to find a real entrepreneur is by googling them. If they truly have run businesses in the past, that were actually businesses, you’ll find references to them on the web. Entrepreneurs that have actually built things will be proud of their accomplishments and create a presence for them on sites like Linkedin and Angel.co.

Forget about Resumes…

Don’t rely on resumes. Most people lie on resumes, or stretch the truth to questionable length. They do this because they’re always trying to sound better than they are. Instead, check out someone’s Linkedin profile. See what roles they’ve listed and what other people have said about them. This will get you much greater insight than a resume of lies.

Try Before you Buy

If you find someone that seems to be a fit, give them a small test project to see how they perform. Most entrepreneurs love this sort of challenge, and will jump at the opportunity to show what they can do. This mitigates some risk and helps both parties get a feel for what it’s like to work together.

I hope this inspires you to rethink how you hire for your startup. Luckily for us, there’s plenty of entrepreneurial people out there, and the supply continues to increase, so the toughest part is finding them! Good luck with your search.